Winsted, CT Residential Income Properties for Sale

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Multifamily and Office Space Opportunity

$319,900

2,754 SF

Multifamily and Office Space Opportunity

25 Center St, Winchester, CT 06098

Multifamily residential property with office space in central location.

Opportunity to own a multifamily residential property with additional office space.
Potential to create a 2nd residential unit on the first floor (town permission granted).
Prime central location near restaurants, parks, college, public transportation, and shopping in Winsted.
Includes two electric meters and two 50‑gallon hot water tanks.
First floor available 'as is', offering customization potential.

Updated: Jan 30

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$750,000

5,389 SF

Turnkey Restaurant with Apartments

436 Main St, Winchester, CT 06098

Thriving restaurant with apartments in high-traffic Litchfield County location.

Turnkey, award‑winning restaurant with a 10‑year track record and loyal customer base.
Prime location in the heart of Litchfield County with high traffic.
Includes 4 apartments in addition to the restaurant.
Restaurant recognized in top publications including the New York Times and Wall Street Journal.
Fully equipped restaurant with all infrastructure items included (valued over $100k).

Updated: Oct 27, 2025

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Downtown Winchester Redevelopment Opportunity

Pending

$99,000

4,679 SF

Downtown Winchester Redevelopment Opportunity

Redevelopment opportunity in downtown Winchester with retail and residential potential.

508 Main St, Winchester, CT 06098

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Winchester Multi-Family Investment Opportunity

Pending

$299,900

1,874 SF

Winchester Multi-Family Investment Opportunity

Three-unit property with long-term tenants and vacant unit.

106 Rockwell St, Winchester, CT 06098

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$395,000

1,909 SF

Mixed-Use Building in Downtown Winsted

Two-story building with commercial space and residential apartment.

720 Main St, Winchester, CT 06098

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$395,000

1,909 SF

Mixed-Use Building in Downtown Winsted

Two-story building with commercial space and renovated apartment.

720 Main St, Winchester, CT 06098

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Pending

$299,900

2,699 SF

Updated Two-Family Winchester Residence

Two-family residence with modern updates and income potential.

77 Hubbard St, Winchester, CT 06098

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$225,000

Litchfield County Two-Family Home

Two-family home in Litchfield County with income potential.

30 Rock St, Winchester, CT 06098

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$349,900

Well-Maintained Two-Family Home

Two-family home with detached garage, convenient location.

135 Elm St, Winchester, CT 06098

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$259,000

Multifamily Home Near Transportation

Multifamily home with spacious rooms, storage, and convenient transportation.

10 Crescent St, Winchester, CT 06098

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Based on your search, we've compiled 44 Potential Opportunities for your consideration. Besides 10 Active listings in Winsted, CT, we suggest exploring several alternatives: 4 properties in Nearby Cities, and similar 28 Off-Market properties to explore as potential leads, plus 2 Land Listings that present a potential for development.

Explore Opportunities in Nearby Cities

Here are 4 Similar properties we found in Nearby Locations for your consideration.

Torrington, CT 6-Unit Apartment Building

$1,195,000

5,000 SF

Torrington, CT 6-Unit Apartment Building

Brand new, 6-unit apartment complex, ready March 2025.

775 Main St, Torrington, CT 06790

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$469,900

Renovated Duplex with Garage Bays

Side-by-side duplex renovated in 2022 with modern amenities.

25 Margerie St, Torrington, CT 06790

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$499,000

6,944 SF

Mixed-Use Property in Central Goshen

Mixed-use property on over 3 acres in central Goshen.

78 North St, Goshen, CT 06756

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$4,450,000

294.00 Acres

Goshen, CT Residential Land - 294 Acres

Prime Connecticut Land: Private Pond, Wooded

0 Reservoir Rd, Goshen, CT 06756

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Potential Development Sites for Consideration

Can't find the perfect fit? These Land listings present an alternative path: the potential to develop a property for your specific goals.

Important: These AI-suggestions are a starting point, not a guarantee of permitted use. All zoning, permitting, and land use information must be independently verified by you with the appropriate local authorities before making any commitments.

$299,900

63.00 Acres

63 Acres Abutting State Forest

63-acre wooded land parcel abutting Algonquin State Forest.

32 Norfolk Rd, Winchester, CT 06098

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$879,990

131.50 Acres

Rare Multi-Parcel Land Opportunity

Five contiguous parcels in Winchester and Colebrook, Connecticut.

APARTMENT HOUSE (UNDER 5 UNITS) • 5.01 Acres

Value Estimation

$2,450,000

69 Pleasant Vly Rd, Barkhamsted, CT 06063-4008

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4 Riv Rd

APARTMENT HOUSE (UNDER 5 UNITS) • 3,676 SF

Value Estimation by Request

4 Riv Rd, Barkhamsted, CT 06063-4000

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19 Ctr St

APARTMENT HOUSE (UNDER 5 UNITS) • 0.18 Acres

Value Estimation by Request

19 Ctr St, Winsted, CT 06098-1611

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137 Gilbert Ave

APARTMENT HOUSE (UNDER 5 UNITS) • 3,493 SF

Value Estimation by Request

137 Gilbert Ave, Winsted, CT 06098-1317

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91 Torringford St

APARTMENT HOUSE (UNDER 5 UNITS) • 1.54 Acres

Value Estimation

$670,000

91 Torringford St, Winsted, CT 06098-2000

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149 Mdw St, Unit 155

APARTMENT HOUSE (UNDER 5 UNITS) • 4,798 SF

Value Estimation by Request

149 Mdw St, Winsted, CT 06098-1015

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143 Main St

APARTMENT HOUSE (UNDER 5 UNITS) • 2,756 SF

Value Estimation by Request

143 Main St, Winsted, CT 06098-1281

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6 Brk St

APARTMENT HOUSE (UNDER 5 UNITS) • 3,400 SF

Value Estimation by Request

6 Brk St, Winsted, CT 06098

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106 Elm St, Unit 112

APARTMENT HOUSE (UNDER 5 UNITS) • 2,712 SF

Value Estimation by Request

106 Elm St, Winsted, CT 06098-1637

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Winsted, CT Residential Income Properties Investment Opportunities Market Analysis

Explore 38 residential income properties for sale in Winsted, CT, showcased through 10 active listings on our real estate platform. These investment opportunities span a total of 782,338 square feet of properties for sale, with an estimated market value of $13,483,700.

Prices for residential income properties in Winsted, CT start at $99,000, averaging $408,596, and reaching up to $2,695,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you have the most current data.

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Winsted, CT Residential Income Properties for Sale

Multifamily and Office Space Opportunity

Multifamily residential property with office space in central location.

Turnkey Restaurant with Apartments

Thriving restaurant with apartments in high-traffic Litchfield County location.

Downtown Winchester Redevelopment Opportunity

Winchester Multi-Family Investment Opportunity

Mixed-Use Building in Downtown Winsted

Mixed-Use Building in Downtown Winsted

Updated Two-Family Winchester Residence

Litchfield County Two-Family Home

Well-Maintained Two-Family Home

Multifamily Home Near Transportation

Explore Opportunities in Nearby Cities

Torrington, CT 6-Unit Apartment Building

Renovated Duplex with Garage Bays

Mixed-Use Property in Central Goshen

Goshen, CT Residential Land - 294 Acres

Potential Development Sites for Consideration

63 Acres Abutting State Forest

Rare Multi-Parcel Land Opportunity

Explore Off-Market Properties in Winsted, CT

155 Gilbert Ave

61 Holabird Ave

175 Main St

109-111 Holabird Ave, Unit 111

157 Prospect St

69 Pleasant Vly Rd

4 Riv Rd

19 Ctr St

137 Gilbert Ave

91 Torringford St

149 Mdw St, Unit 155

143 Main St

6 Brk St

106 Elm St, Unit 112

Winsted, CT Residential Income Properties Investment Opportunities Market Analysis

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